Condensed cyclic compound and organic light-emitting device including the same

ABSTRACT

A condensed-cyclic compound represented by Formula 1A: 
     
       
         
         
             
             
         
       
         
         
           
             wherein in Formula 1A, groups, substituents, and variables are the same as defined in the specification.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of U.S. patent applicationSer. No. 14/573,422, filed on Dec. 17, 2014, which claims priority toKorean Patent Application No. 10-2013-0157532, filed on Dec. 17, 2013,and all the benefits accruing therefrom under 35 U.S.C. § 119, thecontents of which are incorporated herein in their entireties byreference.

BACKGROUND 1. Field

One or more embodiments of the present disclosure relate tocondensed-cyclic compounds and organic light-emitting devices includingthe condensed-cyclic compounds.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emitting devices thathave advantages such as wide viewing angles, excellent contrast ratios,and quick response times. In addition, OLEDs exhibit excellentbrightness, driving voltage, and response speed characteristics, and canprovide multicolored images.

A typical OLED has a structure including an anode, a cathode, and anorganic layer disposed between the anode and the cathode and includingan emission layer. A hole transporting region may be disposed betweenthe anode and the cathode, and an electron transporting region may bedisposed between the emission layer and the cathode. Holes injected fromthe anode move to the EML via the hole transport region, and electronsinjected from the cathode move to the EML via the electron transportregion. Carriers such as holes and electrons recombine in the EML togenerate excitons. When the excitons drop from an excited state to aground state, light is emitted.

Different types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

One or more embodiments include novel condensed-cyclic compounds andorganic light-emitting devices including the condensed-cyclic compounds.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

According to one or more embodiments, provided is a condensed-cycliccompound represented by Formula 1A or 1B:

In the Formulae above,

ring A₁ in Formulae 1A and 1B is represented by Formula 1C or 1D;

X₁ is N or C-[(L₁)_(a1)-(R₁)_(b1)],

X₂ is N or C-[(L₂)_(a2)-(R₂)_(b2)],

X₃ is N or C-[(L₃)_(a3)-(R₃)_(b3)], and

at least one of X₁ to X₃ is N;

X₄ is O or S;

X₁₁ is selected from N-[(L₁₂)_(a12)-(R₁₂)_(b12)], S, O, S(═O), S(═O)₂,C(═O), C(R₁₃)(R₁₄), Si(R₁₃)(R₁₄), P(R₁₃), P(═O)(R₁₃), and C═N(R₁₂);

L₁ to L₄, L₁₁, L₁₂ and L₂₁ may be each independently selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substitutedor unsubstituted C₂-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₂-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic hetero-condensed polycyclic group;

a1 to a4, a11, a12, and a21 may be each independently selected fromintegers of 0 to 3;

R₁ to R₃, R₅, R₆, and R₁₁ to R₁₇ may be each independently selected froma hydrogen, a deuterium, —F (a fluoro group), —Cl (a chloro group), —Br(a bromo group), —I (an iodo group), a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic hetero-condensed polycyclic group,—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇),

R₄ is selected from a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic hetero-condensedpolycyclic group;

b1 to b6 and b11 to b17 may be each independently selected from integersof 1 to 3;

at least one substituent of the substituted C₃-C₁₀ cycloalkylene group,substituted C₂-C₁₀ heterocycloalkylene group, substituted C₃-C₁₀cycloalkenylene group, substituted C₂-C₁₀ heterocycloalkenylene group,substituted C₆-C₆₀ arylene group, substituted C₂-C₆₀ heteroarylenegroup, substituted divalent non-aromatic condensed polycyclic group,substituted divalent non-aromatic hetero-condensed polycyclic group,substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀ cycloalkyl group, substituted C₂-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₂-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₂-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatichetero-condensed polycyclic group may be selected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromatichetero-condensed polycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅) and—B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic hetero-condensed polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic hetero-condensed polycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromatichetero-condensed polycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅) and —B(Q₃₆)(Q₃₇);

wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇, and Q₃₁ to Q₃₇ may be eachindependently selected from a hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group,monovalent a non-aromatic condensed polycyclic group, and a monovalentnon-aromatic hetero-condensed polycyclic group.

According to one or more other embodiments, provided is acondensed-cyclic compound represented by Formula 1A:

wherein in Formula 1A,

ring A₁ is represented by Formula 1D;

X₁ to X₃ is N;

X₄ is O or S;

L₄ and L₂₁ are each independently selected from groups represented byFormulae 2-1, 2-2 and 2-34;

wherein in Formulae 2-1, 2-2 and 2-34, Z₁ is selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group and a phenyl group and d1 is selected from integersof 1 to 4;

a4 is selected from integers 0 to 3 and a21 is 0, 1, 2 or 3;

R₅, R₆, R₁₅ and R₁₇ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, anda C₁-C₂₀ alkoxy group;

R₄ is selected from:

a phenyl group; and

a phenyl group, substituted with at least one of a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoricacid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, and a biphenyl group; and

b4 to b6, b15 and b17 are each independently selected from integers of 1to 3.

According to one or more other embodiments, provided is an organiclight-emitting device including

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode,

wherein the organic layer includes an emission layer and at least onecondensed-cyclic compound described above.

The condensed-cyclic compound may be included in the emission layer,wherein the emission layer further includes a dopant, and thecondensed-cyclic compound included in the emission layer may act as ahost.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the accompanying drawing in which:

the FIGURE is a schematic view showing an organic light-emitting deviceaccording to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to the like elements throughout. In this regard, thepresent embodiments may have different forms and should not be construedas being limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the FIGURES, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” It will be further understood that theterms “comprises” and/or “comprising,” or “includes” and/or “including”when used in this specification, specify the presence of statedfeatures, regions, integers, steps, operations, elements, and/orcomponents, but do not preclude the presence or addition of one or moreother features, regions, integers, steps, operations, elements,components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

A condensed-cyclic compound according to an embodiment may berepresented by Formula 1A or 1B:

ring A₁ in Formula 1A and 1B may be represented by Formula 1C or 1D.

In Formulae 1A and 1B, ring A₁ may be fused with an adjacent 5-memberedcyclic ring by sharing the carbon atoms disposed therebetween.Accordingly, the condensed-cyclic compound represented by Formula 1A or1B may be represented by any one of Formulae 1A-1 to 1A-7 and 1B-1 to1B-4:

Descriptions of Formulae 1A-1 to 1A-7 and 1B-1 to 1B-4, X₁ to X₄, X₁₁,L₁ to L₄, L₁₁, L₁₂, L₂₁, a1 to a4, a11, a12, a21, R₁ to R₆, R₁₁ to R₁₇,b1 to b6, and b11 to b17 are given below.

According to an embodiment, the condensed-cyclic compound may berepresented by Formula 1A-1, 1A-2, 1A-3, 1B-1, 1B-2, 1B-3, or 1B-4, butit is not limited thereto.

According to another embodiment, the condensed-cyclic compound may berepresented by Formula 1A-1 or 1A-2, but it is not limited thereto.

Formulae 1A and 1B may be represented by any one of Formulae 1A(1) to1A(4) and 1B(1) to 1B(4), but they are not limited thereto:

In Formulae 1A(1) to 1A(4) and 1B(1) to 1B(4), descriptions of ring A₁,X₁ to X₄, X₁₁, L₁ to L₄, L₁₁, L₁₂, L₂₁, a1 to a4, a11, a12, a21, R₁ toR₆, R₁₁ to R₁₇, b1 to b6, and b11 to b17 are given below.

In Formula 1C, X₁₁ is selected from N-[(L₁₂)_(a12)-(R₁₂)_(b12)], S, O,S(═O), S(═O)₂, C(═O), C(R₁₃)(R₁₄), Si(R₁₃)(R₁₄), P(R₁₃), P(═O)(R₁₃), andC═N(R₁₂). For example, in Formula 1C, X₁₁ may be selected fromN-[(L₁₂)_(a12)-(R₁₂)_(b12)], S, O, and C(R₁₃)(R₁₄), but it is notlimited thereto. Descriptions of L₁₂, a12, R₁₂ to R₁₄, and b12 may beunderstood by referring to the description below.

In Formula 1A and 1B, X₁ is N or C-[(L₁)_(a1)-(R₁)_(b1)], X₂ is N orC-[(L₂)_(a2)-(R₂)_(b2)], X₃ is N or C-[(L₃)_(a3)-(R₃)_(b3)], and atleast one of X₁ to X₃ is N.

For example, in Formulae 1A and 1B,

X₁ to X₃ may be N;

X₁ may be C-[(L₁)_(a1)-(R₁)_(b1)], X₂ and X₃ may be N;

X₁ may be N, X₂ may be C-[(L₂)_(a2)-(R₂)_(b2)], and X₃ may be N;

X₁ and X₂ may be N, and X₃ may be C-[(L₃)_(a3)-(R₃)_(b3)];

X₁ may be C-[(L₁)_(a1)-(R₁)_(b1)], X₂ may be N, and X₃ may beC-[(L₃)_(a3)-(R₃)_(b3)];

X₁ may be C-[(L₁)_(a1)-(R₁)_(b1)], X₂ may be C-[(L₂)_(a2)-(R₂)_(b2)],and X₃ may be N; or

X₁ may be N, X₂ may be C-[(L₂)_(a2)-(R₂)_(b2)], and X₃ may beC-[(L₃)_(a3)-(R₃)_(b3)]

According to an embodiment,

X₁ may be C-[(L₁)_(a1)-(R₁)_(b1)], X₂ and X₃ may be N; or

X₁ and X₂ may be N, and X₃ may be C-[(L₃)_(a3)-(R₃)_(b3)], but they arenot limited thereto.

Descriptions of L₁ to L₃, a1 to a3, R₁ to R₃, and b1 to b3 may beunderstood by referring to the description below.

In Formulae 1A, 1B, and 1C, L₁ to L₄, L₁₁, L₁₂, and L₂₁ may be eachindependently selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₂-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic hetero-condensed polycyclic group.

For example, in Formulae 1A, 1B, and 1C, L₁ to L₄, L₁₁, Lie, and L₂₁ maybe each independently selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthrenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pyrrolylene group, animidazolylene group, a pyrazolylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, anisoindolylene group, an indolylene group, an indazolylene group, apurinylene group, a quinolinylene group, an isoquinolinylene group, abenzoquinolinylene group, a phthalazinylene group, a naphthyridinylenegroup, a quinoxalinylene group, a quinazolinylene group, a cinnolinylenegroup, a carbazolylene group, a phenanthridinylene group, anacridinylene group, a phenanthrolinylene group, a phenazinylene group, abenzooxazolylene group, a benzoimidazolylene group, a furanylene group,a benzofuranylene group, a thiophenylene group, a benzothiophenylenegroup, a thiazolylene group, a isothiazolylene group, abenzothiazolylene group, an isoxazolylene group, an oxazolylene group, atriazolylene group, a tetrazolylene group, an oxadiazolylene group, atriazinylene group, a dibenzofuranylene group, a dibenzothiophenylenegroup, a benzocarbazolylene group, a dibenzocarbazolylene group, animidazopyrimidinylene group, and an imidazopyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthrenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pyrrolylene group, animidazolylene group, a pyrazolylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, anisoindolylene group, an indolylene group, an indazolylene group, apurinylene group, a quinolinylene group, an isoquinolinylene group, abenzoquinolinylene group, a phthalazinylene group, a naphthyridinylenegroup, a quinoxalinylene group, a quinazolinylene group, a cinnolinylenegroup, a carbazolylene group, a phenanthridinylene group, anacridinylene group, a phenanthrolinylene group, a phenazinylene group, abenzooxazolylene group, a benzoimidazolylene group, a furanylene group,a benzofuranylene group, a thiophenylene group, a benzothiophenylenegroup, a thiazolylene group, a isothiazolylene group, abenzothiazolylene group, an isoxazolylene group, an oxazolylene group, atriazolylene group, a tetrazolylene group, an oxadiazolylene group, atriazinylene group, a dibenzofuranylene group, a dibenzothiophenylenegroup, a benzocarbazolylene group, a dibenzocarbazolylene group animidazopyrimidinylene group, and an imidazopyridinylene group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a C₆-C₂₀ aryl group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromatichetero-condensed cyclic group, and —Si(Q₃₃)(Q₃₄)(Q₃₅),

Q₃₃ to Q₃₅ may be each independently selected from a hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenylgroup, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, acinnolinyl group, and a quinazolinyl group, but they are not limitedthereto.

For example, in Formulae 1A, 1B, and 1C, L₁ to L₄, L₁₁, Lie, and L₂₁ maybe each independently selected from Formulae 2-1 to 2-34:

In Formula 2-1 to 2-34,

Y₁ may be selected from O, S, S(═O), S(═O)₂, C(Z₃)(Z₄), N(Z₅), orSi(Z₆)(Z₇);

Z₁ to Z₇ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenylgroup, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, afluorenyl group, a chrysenyl group, a carbazolyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinazolinyl group, a quinoxalinyl group, a biphenyl group, and—Si(Q₃₃)(Q₃₄)(Q₃₅);

wherein Q₃₃ to Q₃₅ may be each independently selected from a hydrogen, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, afluorenyl group, a chrysenyl group, a carbazolyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinazolinyl group, and a quinoxalinyl group;

d1 is selected from integers of 1 to 4,

d2 is selected from integers of 1 to 3,

d3 is selected from integers of 1 to 6,

d4 is selected from integers of 1 to 8,

d5 is 1 or 2,

d6 is selected from integers of 1 to 5, and

each of * and *′ indicates a bonding site to neighboring atoms.

For example, in Formulae 2-1 to 2-34, *′ indicates a bonding site toneighboring atoms of L₁ to L₄, L₁₁, L₁₂, and L₂₁ or bonding site to eachof R₁ to R₄, R₁₁, R₁₂, and R₂₁.

According to an embodiment, in Formulae 1A and 1B, L₁ to L₄, L₁₁, L₁₂,and L₂₁ may be each independently selected from Formulae 2-1 to 2-5, 2-9to 2-23, and 2-34, but they are not limited thereto.

According to another embodiment, in Formulae 1A and 1B, L₁ to L₄, L₁₁,L₁₂, and L₂₁ may be each independently selected from:

a phenylene group and a naphthylene group; and

a phenylene group and a naphthylene group, each substituted with atleast one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthylgroup, an anthracenyl group, a triphenylenyl group, a pyrenyl group, aphenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, abiphenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅) (wherein Q₃₃ to Q₃₅ may be eachindependently selected from a hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, apyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenylgroup, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group, butthey are not limited thereto.

In Formula 1A, a1 represents the number of groups L₁, which may be 0, 1,2, or 3, for example, 0, 1, or 2, or may be 0 or 1. When a1 is 0,-(L₁)_(a1)- is a single bond. When a1 is 2 or greater, two or moregroups L₁ may be the same or different. Descriptions of a2 to a4, a11,a12, and a21 may be understood by referring to the description of a1 andstructures of Formulae 1A and 1B.

According to an embodiment, in Formulae above, a1 to a4, a11, a12, anda21 may be each independently, 0, 1, or 2.

According to another embodiment, in Formulae above, a21 may be 1, but itis not limited thereto.

In Formulae 1A, 1B, 1C, and 1D, R₁ to R₃, R₅, R₆, and R₁₁ to R₁₇ may beeach independently selected from a hydrogen, a deuterium, —F (a fluorogroup), —Cl (a chloro group), —Br (a bromo group), —I (an iodo group), ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic hetero-condensedpolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇). Here,descriptions of Q₁ to Q₇ are as described below.

In Formulae 1A and 1B, R₄ is selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic hetero-condensed polycyclic group.For example, R₄ may be selected from a substituted or unsubstitutedC₆-C₂₀ aryl group, a substituted or unsubstituted C₂-C₃₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic hetero-condensed polycyclic group, but it is not limitedthereto.

According to an embodiment, in Formulae 1A and 1B, R₁₁ and R₁₇ may beeach independently selected from a substituted or unsubstituted C₆-C₃₀aryl group, a substituted or unsubstituted C₂-C₃₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic hetero-condensed polycyclic group.

For example, in Formulae 1A, 1B, 1C, and 1D, R₁ to R₃, R₅, R₆, and R₁₃to R₁₇ may be each independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof and a phosphoric acid or a salt thereof;

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group;

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, —Si(Q₃₃)(Q₃₄)(Q₃₅), a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, and a biphenyl group; and

—Si(Q₃)(Q₄)(Q₅) (provided that, R₁₃ and R₁₄ are not —Si(Q₃)(Q₄)(Q₅));

wherein Q₃ to Q₅ and Q₃₃ to Q₃₅ may be each independently selected froma hydrogen, C₁-C₂₀ alkyl group, C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenylgroup, a fluorenyl group, a chrysenyl group, a carbazolyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinazolinyl group, and a quinoxalinyl group, but they are not limitedthereto.

According to another embodiment, in Formulae 1A, 1B, 1C, and 1D, R₁ toR₃, R₅, R₆, and R₁₃ to R₁₇ may be each independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, and a phosphoric acid or a saltthereof;

a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenylgroup, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, achrysenyl group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, aquinolinyl group, an isoquinolinyl group, a quinazolinyl group, and aquinoxalinyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenylgroup, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, achrysenyl group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, aquinolinyl group, an isoquinolinyl group, a quinazolinyl group, and aquinoxalinyl group, each substituted with at least one of a deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, —Si(Q₃₃)(Q₃₄)(Q₃₅), a phenyl group, a naphthyl group, ananthracenyl group, a triphenylenyl group, a pyrenyl group, aphenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group; and

—Si(Q₃)(Q₄)(Q₅), provided that R₁₃ and R₁₄ are not —Si(Q₃)(Q₄)(Q₅);

wherein Q₃ to Q₅ and Q₃₃ to Q₃₅ may be each independently selected froma hydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group,a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenylgroup, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, acarbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group.

Meanwhile, in Formulae 1A and 1B, R₄, R₁₁, and R₁₂ may be eachindependently selected from:

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group; and

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group and animidazopyrimidinyl group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, —Si(Q₃₃)(Q₃₄)(Q₃₅), a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, and a biphenyl group; and

Q₃₃ to Q₃₅ may be each independently selected from a hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, ananthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenylgroup, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, aquinolinyl group, an isoquinolinyl group, a quinazolinyl group, and aquinoxalinyl group.

According to another embodiment, in Formulae 1A, 1B, 1C, and 1D,

R₁ to R₃, R₅, R₆, and R₁₃ to R₁₇ may be each independently selectedfrom:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

-   -   a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted        with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl        group, a cyano group, a nitro group, an amino group, an amidino        group, a hydrazine group, a hydrazone group, a carboxylic acid        or a salt thereof, a sulfonic acid or a salt thereof, and a        phosphoric acid or a salt thereof;

Formulae 4-1 to 4-31 below (for example, Formulae 4-1 to 4-3 and 4-6 to4-13); and

—Si(Q₃)(Q₄)(Q₅) (provided that, R₁₃ and R₁₄ are not —Si(Q₃)(Q₄)(Q₅));

wherein, R₄, R₁₁, and R₁₇ may be each independently selected fromFormulae 4-1 to 4-31 (for example, Formulae 4-1 to 4-3 and 4-6 to 4-13),but they are not limited thereto.

In Formulae 4-1 to 4-31,

Y₃₁ may be O, S, C(Z₃₃)(Z₃₄), N(Z₃₅) or Si(Z₃₆)(Z₃₇),

Z₃₁ to Z₃₇ may be each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, C₁-C₂₀ alkyl group, C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, atriphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenylgroup, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, aquinolinyl group, an isoquinolinyl group, a quinazolinyl group, aquinoxalinyl group, a biphenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅);

Q₃ to Q₅ and Q₃₃ to Q₃₅ may be each independently selected from ahydrogen, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenylgroup, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, acarbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group;

e1 may be selected from integers of 1 to 5,

e2 is selected from integers of 1 to 7,

e3 is selected from integers of 1 to 3,

e4 is selected from integers of 1 to 4,

e5 is 1 or 2,

e6 is selected from integers of 1 to 6, and

* indicates a bonding site to a neighboring atom.

According to another embodiment, R₁ to R₃, R₅, R₆, and R₁₃ to R₁₇ may beeach independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, and a phosphoric acid or a saltthereof;

a phenyl group and a naphthyl group;

a phenyl group and a naphthyl group, each substituted with at least oneof a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, and a naphthyl group; and

—Si(Q₃)(Q₄)(Q₅) (provided that, R₁₃ and R₁₄ are not —Si(Q₃)(Q₄)(Q₅) andQ₃ to Q₅ are each independently selected from a hydrogen, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, and a naphthyl group);

R₄, R₁₁, and R₁₂ are each independently selected from:

a phenyl group and a naphthyl group; and

a phenyl group and a naphthyl group, each substituted with at least oneof a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, and a naphthyl group; but,they are not limited thereto.

According to another embodiment, R₅, R₆, and R₁₅ to R₁₇ may all behydrogen, but they are not limited thereto.

In Formulae 1A and 1B, b1 represents the number of groups R₁ and may beselected from integers of 1 to 3. For example, b1 may be 1 or 2. Ingreater detail, b1 may be 1. When b1 is 2 or greater, two or more ofgroups R₁ may be the same or different. Descriptions of b2 to b6 and b11to b17 may be understood by referring to the description of b1 andstructures of Formulae 1A, 1B, 1C, and 1D.

According to an embodiment, at least one substituent of the substitutedC₃-C₁₀ cycloalkylene group, substituted C₂-C₁₀ heterocycloalkylenegroup, substituted C₃-C₁₀ cycloalkenylene group, substituted C₂-C₁₀heterocycloalkenylene group, substituted C₆-C₆₀ arylene group,substituted C₂-C₆₀ heteroarylene group, substituted divalentnon-aromatic condensed polycyclic group, substituted divalentnon-aromatic hetero-condensed polycyclic group, substituted C₁-C₆₀ alkylgroup, substituted C₂-C₆₀ alkenyl group, substituted C₂-C₆₀ alkynylgroup, substituted C₁-C₆₀ alkoxy group, substituted C₃-C₁₀ cycloalkylgroup, substituted C₂-C₁₀ heterocycloalkyl group, substituted C₃-C₁₀cycloalkenyl group, substituted C₂-C₁₀ heterocycloalkenyl group,substituted C₆-C₆₀ aryl group, substituted C₆-C₆₀ aryloxy group,substituted C₆-C₆₀ arylthio group, substituted C₂-C₆₀ heteroaryl group,substituted monovalent non-aromatic condensed polycyclic group, andsubstituted monovalent non-aromatic hetero-condensed polycyclic groupmay be selected from:

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₃-C₁₀ cycloalkyl group,a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromatichetero-condensed polycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅) and—B(Q₁₆)(Q₁₇);

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic hetero-condensed polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic hetero-condensed polycyclic group, eachsubstituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromatichetero-condensed polycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and—B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅) and —B(Q₃₆)(Q₃₇);

wherein Q₁ to Q₇, Q₁₁ to Q₁₇, Q₂₁ to Q₂₇ and Q₃₁ to Q₃₇ may be eachindependently selected from a hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₂-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₂-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic hetero-condensed polycyclic group.

According to one or more embodiments, provided is a condensed-cycliccompound represented by Formula 1A:

wherein in Formula 1A,

ring A₁ is represented by Formula 1D;

X₁ to X₃ is N;

X₄ is O or S;

L₄ and L₂₁ are each independently selected from groups represented byFormulae 2-1, 2-2 and 2-34;

wherein in Formulae 2-1, 2-2 and 2-34, Z₁ is selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group and a phenyl group and d1 is selected from integersof 1 to 4;

a4 is selected from integers 0 to 3 and a21 is 0, 1, 2 or 3 (or a21 maybe 1 or 2);

R₅, R₆, R₁₅ and R₁₇ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, anda C₁-C₂₀ alkoxy group;

R₄ is selected from:

a phenyl group; and

a phenyl group, substituted with at least one of a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoricacid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, and a biphenyl group; and

b4 to b6, b15 and b17 are each independently selected from integers of 1to 3.

For example, a condensed-cyclic compound represented by Formula 1Adescribed above may be represented by one of Formulae 1A(1) to 1A(4)described herein.

The condensed-cyclic compound may be any one of Compounds 1 to 825, butit is not limited thereto:

Alternatively, the condensed-cyclic compound may be any one of Compounds1, 85, 169, 253, 337, 421, 505, 506, 575, 659, 660, 729 and 825, but itis not limited thereto:

In the condensed-cyclic compound represented by Formula 1A or 1B, R₄ isselected from a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic hetero-condensedpolycyclic group.

In other words, in Formula 1A and 1B, R₄ necessarily includes a ringstructure. As a result, the condensed-cyclic compound represented byFormula 1A or 1B is chemically and structurally stable and may actuallyhave a spherical molecular structure. Accordingly, the condensed-cycliccompound represented by Formula 1A or 1B may have excellent thermalstability, which may increase deposition temperature. As a result,efficiency and lifespan of an organic light-emitting device includingthe condensed-cyclic compound may be improved to improve formability ofthe organic light-emitting device during the manufacturing processthereof.

Also, because both group “A” and the “carbazole-based” group in Formulae1A and 1B are bound to a “nitrogen-containing 6-membered ring” (seeFormulae 1A′ and 1B′), hole injection and hole transport and electroninjection and electron transport may occur thoroughly and Formulae 1Aand 1B may each actually have a spherical molecular structure.Accordingly, the condensed-cyclic compound may simultaneously haveexcellent charge-transporting ability and thermal stability, such thatthe organic light-emitting device including the condensed-cycliccompound may have increased emission efficiency, reduced drivingvoltage, and a long lifespan.

A method of synthesizing the condensed-cyclic compound represented byFormula 1A or 1B may be understood by one of ordinary skill in the artby referring to the embodiments described below.

Accordingly, the condensed-cyclic compound represented by Formula 1A or1B may be suitable as a material for an organic layer (for example, ahost of an EML) in an organic light-emitting device. According toanother embodiment, provided is an organic light-emitting deviceincluding

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode,

wherein the organic layer includes the EML, which includes at least onecondensed-cyclic compound represented by Formula 1A or 1B.

The organic light-emitting device including an organic layer includingthe condensed-cyclic compound represented by Formula 1A or 1B has lowdriving voltage, high efficiency, high brightness, and a long lifespan.

The condensed-cyclic compound represented by Formula 1A or 1B may beused between a pair of electrodes in the organic light-emitting device.For example, the condensed-cyclic compound may be included in at leastone of an EML, a hole-transport region disposed between the firstelectrode and the EML (for example, the hole transport region mayinclude at least one of a hole-injecting layer (HIL), ahole-transporting layer (HTL), and an electron-blocking layer (EBL)),and an electron-transport region disposed between the EML and the secondelectrode (for example, the electron transport region may include atleast one of a hole-blocking layer (HBL), an electron-transporting layer(ETL), and an electron-injecting layer (EIL)). For example, thecondensed-cyclic compound represented by Formula 1A or 1B may beincluded in the EML. In this regard, the EML further includes a dopantand the condensed-cyclic compound included in the EML may act as a host.The EML may be a green EML emitting green light and the dopant may be aphosphorescent dopant.

As used herein, the term “(the organic layer) includes at least onecondensed-cyclic compound” may be understood as “(the organic layer) mayinclude at least one condensed-cyclic compound belonging to the group ofFormula 1A or 1B or two different condensed-cyclic compounds belongingto the group of Formula 1A or 1B”.

For example, the organic layer may only include Compound 1 as thecondensed-cyclic compound. In this regard, Compound 1 may be situated inthe EML of the organic light-emitting device. Alternatively, the organiclayer may include Compound 1 and Compound 2 as the condensed-cycliccompound. In this regard, Compound 1 and Compound 2 may be present onthe same layer (for example, Compound 1 and Compound 2 may all bepresent on the EML) or on different layers.

The organic layer includes

i) a hole transport region that is disposed between the first electrodeand the EML and includes at least one of an HIL, an HTL, a buffer layer,and an EBL, and

ii) an electron transport region that is disposed between the EML andthe second electrode and includes at least one layer selected from aHBL, an ETL, and an EIL.

The expression “organic layer”, as used herein refers to a single layerand/or a plurality of layers disposed between the first and secondelectrodes of an organic light-emitting device. A material of the“organic layer” is not limited to an organic material and may include anorganic metal complex including a metal.

The FIGURE is a schematic view of an organic light-emitting device 10according to an embodiment. Hereinafter, a structure and a method ofmanufacturing the organic light-emitting device according to anembodiment will be described with reference to the FIGURE. The organiclight-emitting device 10 includes a first electrode 11, an organic layer15, and a second electrode 19, which are sequentially stacked in thestated order.

A substrate may be additionally disposed under the first electrode 11 oron the second electrode 19. The substrate may be a conventional glasssubstrate or a transparent plastic substrate, each with excellentmechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water repellency.

The first electrode 11 may be formed by depositing or sputtering amaterial for forming the first electrode 11 on the substrate. When thefirst electrode 11 is an anode, the material for the first electrode 11may be selected from materials with a high work function for an easyhole injection. The first electrode 11 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. The materialfor the first electrode 110 may be selected from indium tin oxide (ITO),indium zinc oxide (IZO), tin oxide (SnO₂), and zinc oxide (ZnO).Alternatively, a metal such as magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), andmagnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layer structure or amulti-layer structure including two or more layers.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region; an EML; and anelectron transport region.

The hole transport region may be disposed between the first electrode 11and the EML.

The hole transport region may include at least one of the HIL, HTL, EBL,and buffer layer.

The hole transport region may only include the HIL or HTL.Alternatively, the hole transport region may have an HIL/HTL structureor an HIL/HTL/EBL structure, wherein layers of each structure aresequentially stacked on the first electrode 11 in this stated order, butit is not limited thereto.

When the hole transport region includes an HIL, the HIL may be formed onthe first electrode 11 by using various methods, such as vacuumdeposition, spin coating, casting, a Langmuir-Blodgett (LB) method, orthe like.

When an HIL is formed by vacuum deposition, for example, the vacuumdeposition may be performed at a deposition temperature of about 100 toabout 500° C., at a vacuum degree of about 10⁻⁸ to about 10⁻³ torr, andat a deposition rate of about 0.01 Angstrom per second (Å/sec) to about100 Å/sec in consideration of a compound for an HIL to be deposited, andthe structure of an HIL to be formed, but the conditions are not limitedthereto.

When an HIL is formed by spin coating, the spin coating may be performedat a coating rate of about 2,000 revolutions per minute (rpm) to about5,000 rpm, and at a temperature of about 80° C. to 200° C. for removinga solvent after the spin coating, in consideration of a compound for anHIL to be deposited, and the structure of an HIL to be formed, but theconditions are not limited thereto.

The conditions for forming the HTL and EBL may be inferred based on theconditions for forming the HIL.

The hole transport region may include at least one compound selectedfrom m-MTDATA, TDATA, 2-TNATA, NPB, 8-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (Pani/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

In Formula 201, Ar₁₀₁ and Ar₁₀₂ may be each independently selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group, each substituted with at least one ofa deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₂-C₁₀ heterocycloalkyl group, a C₂-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₂-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic hetero-condensed polycyclic group.

In Formula 201, xa and xb may be each independently integers of 0 to 5,or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but they arenot limited thereto.

In Formulae 201 and 202, R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄may be each independently selected from:

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₁₀ alkyl group (for example, a methyl group, an ethylgroup, a propyl group, a butyl group, a pentyl group, and a hexyl group)and a C₁-C₁₀ alkoxy group (for example, a methoxy group, an ethoxygroup, a propoxy group, a butoxy group, and a pentoxy group);

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, and a phosphoric acid group or asalt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group, each substituted with at least one of adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, and a C₁-C₁₀ alkoxy group, but they are not limitedthereto.

In Formula 201, R₁₀₉ may be any one of a phenyl group, a naphthyl group,an anthracenyl group and a pyridinyl group; a phenyl group, a naphthylgroup, an anthracenyl group, and a pyridinyl group, each substitutedwith at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group.

According to an embodiment, the compound represented by Formula 201 maybe represented by Formula 201A, but it is not limited thereto:

In Formula 201A, detailed descriptions of R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ maybe the same as described herein.

For example, the compound represented by Formula 201 and the compoundrepresented by Formula 202 may include Compounds HT1 to HT20, but thecompound is not limited thereto:

A thickness of the hole transport region may be in a range of about 100Angstrom (Å) to about 10,000 Å, for example, about 100 Å to about 1,000Å. When the hole transport region includes an HIL and a HTL, a thicknessof the HIL may be in a range of about 100 Å to about 10,000 Å, forexample, about 100 Å to about 1,000 Å, and a thickness of the HTL may bein a range of about 50 Å to about 2,000 Å, for example, about 100 Å toabout 1,500 Å. When the thicknesses of the hole transport region, theHIL, and the HTL are within these ranges, satisfactory hole transportingcharacteristics may be obtained without a substantial increase indriving voltage.

The hole transport region may further include, in addition to theabovementioned materials, a charge-generating material for theimprovement of conductive properties. The charge-generating material maybe homogeneously or non-homogeneously dispersed throughout the holetransport region.

The charge-generating material may be, for example, a p-dopant. Thep-dopant may be one of a quinone derivative, a metal oxide, and a cyanogroup-containing compound, but is not limited thereto. For example,non-limiting examples of the p-dopant are a quinone derivative, such astetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenum oxide; andCompound HT-D1 illustrated below, but are not limited thereto.

The hole transport region may further include a buffer layer.

The buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the EML, and thus,efficiency of an organic light-emitting device may be improved.

An EML may be formed on the hole transport region by using variousmethods, such as vacuum deposition, spin coating, casting, or an LBmethod. When the EML is formed by vacuum deposition or spin coating,deposition and coating conditions for the EML may be determined byreferring to the deposition and coating conditions for the HIL.

The EML may include a host and a dopant. The host may include at leastone condensed-cyclic compound represented by Formula 1A or 1B.

The host may include at least one compound selected from TPBi, TBADN,ADN (also referred to as “DNA”), CBP, CDBP, and TCP:

When the organic light-emitting device 10 is a full color organiclight-emitting device, the EML may be patterned into a red EML, a greenEML, and a blue EML. In some embodiments, the EML may have a stackedstructure of a red EML, a green EML, and/or a blue EML to emit whitelight. The host in the red EML, green EML, and blue EML may include thecondensed-cyclic compound represented by Formula 1. According to anembodiment, the host in the green EML may include the condensed-cycliccompound represented by Formula 1A or 1B.

The EML may include a fluorescent dopant that emits light according to afluorescent light emission mechanism or a phosphorescent dopant thatemits light according to a phosphorescent light emission mechanism.

According to an embodiment, the EML may include a fluorescent and aphosphorescent dopant including the condensed-cyclic compoundrepresented by Formula 1A or 1B. The phosphorescent dopant may includean organic metal complex including a transition metal (for example,iridium (Ir), platinum (Pt), osmium (Os), rhodium (Rh), or the like).

The phosphorescent compound may include an organometallic compoundrepresented by Formula 81:

In Formula 81,

M may be selected from Iridium (Ir), platinum (Pt), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm);

Y₁ to Y₄ may be each independently carbon (C) or nitrogen (N);

Y₁ and Y₂ may be connected by a single bond or a double bond, and Y₃ andY₄ may be connected by a single bond or a double bond;

CY₁ and CY₂ may be each independently selected from a benzene, anaphthalene, a fluorene, a spiro-fluorene, an indene, a pyrrole, athiopene, a furan, an imidazole, a pyrazole, a thiazole, an isothiazole,an oxazole, an isooxazole, a pyridine, a pyrazine, a pyrimidine, apyridazine, a quinoline, an isoquinoline, a benzoquinoline, aquinoxaline, a quinazoline, a carbazole, a benzoimidazole, benzofuran, abenzothiopene, an isobenzothiopene, a benzooxazole, an isobenzooxazole,a triazole, a tetrazole, an oxadiazole, a triazine, a dibenzofuran, anda dibenzothiopene, wherein CY₁ and CY₂ are optionally bound to eachother via a single bond or an organic linking group;

R₈₁ and R₈₂ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, —SF₅, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic hetero-condensed polycyclic group,—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);

a81 and a82 are each independently selected from integers of 1 to 5;

n81 is selected from integers of 0 to 4;

n82 is 1, 2, or 3; and

L₈₁ is selected from a monovalent organic ligand, a divalent organicligand, and a trivalent organic ligand.

Descriptions of R₈₁ and R₈₂ may be the same as the description of R₅.

The phosphorescent dopant may include at least one of Compounds PD1 toPD74, but it is not limited thereto:

Alternatively, the phosphorescent dopant may include PtOEP or compoundPhGD:

The fluorescent dopant may include at least one of DPVBi, DPAVBi, TBPe,DCM, DCJTB, Coumarin 6, and C545T.

When the EML includes the host and the dopant, an amount of the dopantmay be selected from a range of about 0.01 parts by weight to about 15parts by weight based on 100 parts by weight of the host, but the amountis not limited thereto.

A thickness of the EML may be about 100 Å to about 1,000 Å, for example,about 200 Å to about 600 Å. When the thickness of the EML is within thisrange, excellent light-emission characteristics may be obtained withouta substantial increase in driving voltage.

Then, an electron transport region may be disposed on the EML.

The electron transport region may include at least one layer selectedfrom a HBL, an ETL, and an EIL, but is not limited thereto.

For example, the electron transport region may have an HBL/ETL/EILstructure or an ETL/EIL structure, wherein layers of each structure aresequentially stacked from the EML in the stated order, but is notlimited thereto. The ETL may have a single layer or a multi-layerstructure including two or more different materials.

The conditions for forming the HBL, ETL, and EIL may be understood byreferring to the conditions for forming the HIL.

When the electron transport region includes the HBL, the HBL mayinclude, for example, at least one of BCP and Bphen, but it is notlimited thereto.

A thickness of the HBL may be in a range of about 20 Å to about 1,000 Å,for example, about 30 Å to about 300 Å. When the thickness of the HBL iswithin the range described above, the HBL may have excellent holeblocking characteristics without a substantial increase in drivingvoltage.

The ETL may include at least one of BCP and Bphen, and may furtherinclude at least one of Alq₃, Balq, TAZ, and NTAZ.

Alternatively, the ETL may include at least one of Compound ET1 and ET2,but it is not limited thereto.

A thickness of the ETL may be in a range of about 100 Å to about 1,000Å, for example, about 150 Å to about 500 Å. When the thickness of theETL is within the range described above, the ETL may have satisfactoryelectron transportation characteristics without a substantial increasein driving voltage.

Also, the ETL may further include, in addition to the materialsdescribed above, a metal-containing material.

The metal-containing material may include a L₁ complex. The L₁ complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2.

The electron transport region may include an EIL that allows electronsto be easily provided from the second electrode 19.

The EIL may include at least one compound selected from LiF, NaCl, CsF,Li₂O, and BaO.

A thickness of the EIL may be in a range of about 1 Å to about 100 Å,for example, about 3 Å to about 90 Å. When the thickness of the EIL iswithin the range described above, the EIL may have satisfactory electrontransportation characteristics without a substantial increase in drivingvoltage.

The second electrode 19 is disposed on the organic layer 15 having thestructure described above. The second electrode 19 may be a cathode thatis an electron injection electrode, and in this regard, a material forforming the second electrode 19 may be a material having a low workfunction, and such a material may be a metal, an alloy, an electricallyconductive compound, or a mixture thereof. Detailed examples of thematerial for forming second electrode 19 are lithium (Li), magnesium(Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag). Alternatively,ITO or IZO may be may be used to form a transmissive second electrode 19to manufacture a top emission light-emitting device.

Hereinbefore, the organic light-emitting device has been described withreference to the FIGURE, but is not limited thereto.

A C₁-C₆₀ alkyl group used herein refers to a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms.Detailed examples thereof are a methyl group, an ethyl group, a propylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, apentyl group, an iso-amyl group, and a hexyl group. A C₁-C₆₀ alkyleneused herein refers to a divalent group having the same structure as theC₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group used herein refers to a monovalent grouprepresented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group). Detailedexamples thereof are a methoxy group, an ethoxy group, and anisopropyloxy group.

A C₂-C₆₀ alkenyl group used herein refers to a hydrocarbon group formedby substituting at least one carbon double bond in the middle or at theterminal of the C₂-C₆₀ alkyl group. Detailed examples thereof are anethenyl group, a propenyl group, and a butenyl group. A C₂-C₆₀alkenylene group used herein refers to a divalent group having the samestructure as the C₂-C₆₀ alkenyl group.

A C₂-C₆₀ alkynyl group used herein refers to a hydrocarbon group formedby substituting at least one carbon triple bond in the middle or at theterminal of the C₂-C₆₀ alkyl group. Detailed examples thereof are anethynyl group and a propynyl group. A C₂-C₆₀ alkynylene group usedherein refers to a divalent group having the same structure as theC₂-C₆₀ alkynyl group.

A C₃-C₁₀ cycloalkyl group used herein refers to a monovalent hydrocarbonmonocyclic group having 3 to 10 carbon atoms. Detailed examples thereofare a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, acyclohexyl group, and a cycloheptyl group. A C₃-C₁₀ cycloalkylene groupused herein refers to a divalent group having the same structure as theC₃-C₁₀ cycloalkyl group.

A C₃-C₁₀ heterocycloalkyl group used herein refers to a monovalentmonocyclic group having at least one heteroatom selected from N, O, P,and S as a ring-forming atom and 3 to 10 carbon atoms. Detailed examplesthereof are tetrahydrofuranyl and tetrahydrothiophenyl. A C₃-C₁₀heterocycloalkylene group used herein refers to a divalent group havingthe same structure as the C₃-C₁₀ heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least one doublebond in the ring thereof and does not have aromaticity. Detailedexamples thereof are a cyclopentenyl group, a cyclohexenyl group, and acycloheptenyl group. A C₃-C₁₀ cycloalkenylene group used herein refersto a divalent group having the same structure as the C₃-C₁₀ cycloalkenylgroup.

A C₂-C₁₀ heterocycloalkenyl group used herein refers to a monovalentmonocyclic group that has at least one heteroatom selected from N, O, P,and S as a ring-forming atom, 2 to 10 carbon atoms, and at least onedouble bond in its ring. Detailed examples of the C₂-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a2,3-dihydrothiophenyl group. A C₂-C₁₀ heterocycloalkenylene group usedherein refers to a divalent group having the same structure as theC₂-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group used herein refers to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Detailedexamples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other.

A C₂-C₆₀ heteroaryl group used herein refers to a monovalent grouphaving a carbocyclic aromatic system that has at least one heteroatomselected from N, O, P, and S as a ring-forming atom, and 2 to 60 carbonatoms. A C₂-C₆₀ heteroarylene group used herein refers to a divalentgroup having a carbocyclic aromatic system that has at least oneheteroatom selected from N, O, P, and S as a ring-forming atom, and 2 to60 carbon atoms. Detailed examples of the C₂-C₆₀ heteroaryl group are apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup. When the C₂-C₆₀ heteroaryl group and the C₂-C₆₀ heteroarylenegroup each include two or more rings, the rings may be fused to eachother.

A C₆-C₆₀ aryloxy group used herein indicates —OA₁₀₂ (wherein A₁₀₂ is theC₆-C₆₀ aryl) and a C₆-C₆₀ arylthio group used herein indicates —SA₁₀₃(wherein A₁₀₃ is the C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group (for example,having 8 to 60 carbon atoms) used herein refers to a monovalent groupthat has two or more rings condensed to each other, only carbon atoms asring-forming atoms, wherein the molecular structure as a whole isnon-aromatic. A detailed example of the monovalent non-aromaticcondensed polycyclic group is a fluorenyl group. A divalent non-aromaticcondensed polycyclic group used herein refers to a divalent group havingthe same structure as the monovalent non-aromatic condensed polycyclicgroup.

A monovalent non-aromatic condensed heteropolycyclic group (for example,having 2 to 60 carbon atoms) used herein refers to a monovalent groupthat has two or more rings condensed to each other, has a heteroatomselected from N, 0 P, and S, other than carbon atoms, as a ring formingatom, wherein the molecular structure as a whole is non-aromatic.Detailed examples of the monovalent non-aromatic condensedheteropolycyclic group are a carbazolyl group. A divalent non-aromaticcondensed heteropolycyclic group used herein refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedheteropolycyclic group.

Hereinafter, an organic light-emitting device according to an embodimentwill be described in detail with reference to Synthesis Examples andExamples. The wording “B was used instead of A” used in describingSynthesis Examples means that a molar equivalent of A was identical to amolar equivalent of B.

EXAMPLE Synthesis Example 1: Synthesis of Compound 813 Synthesis ofIntermediate B

44.0 g (224.3 mmol) of Intermediate A, 126.9 g (224.3 mmol) ofacetophenone, and 9.0 g (224.3 mmol) of sodium hydroxide were added in670 mL of ethanol in a 1,000 mL round bottom flask and then stirred innitrogen atmosphere for 2 hours at room temperature to prepare amixture. Crystallized solids in the mixture were filtered to obtainIntermediate B (59.2. g and yield 88.0%). Element analysis results ofIntermediate B are as follows.

calcd. C₂₁H₁₄O₂: C, 84.54; H, 4.73; 0, 10.73; found: C, 84.51; H, 4.75;O, 10.71.

Synthesis of Intermediate C

13.0 g (106.2 mmol) of Intermediate B, 30.0 g (127.4 mmol) of3-bromobenzimidamide, and 8.5 g (212.3 mmol) of sodium hydroxide wereadded in 500 ml of ethanol in a 1,000 mL round bottom flask, heated in anitrogen atmosphere for 15 hours to reflux the same to prepare amixture. Crystallized solids in the mixture were stirred with water andthen filtered. The crystallized solids were stirred again by usingethanol and then filtered to obtain Intermediate C (23.8 g, yield 47%).Element analysis results of the Intermediate C are as follows.

calcd. C₂₈H₁₇BrN₂O: C, 70.45; H, 3.59; Br, 16.74; N, 5.87; O, 3.35;found C, 70.43; H, 3.60; Br, 16.72; N, 5.85; O, 3.36.

Synthesis of Compound 813

23.8 g (49.9 mmol) of Intermediate C, 7.0 g (41.6 mmol) of 9H-carbazole,8.0 g (83.1 mmol) of sodium t-butoxide, 3.8 g (4.2 mmol) of Pd(dba)₂,and 4.2 mL (8.3 mmol) of tri-t-butyl phosphine (50% in toluene solution)were added to 166.2 mL of xylene in a 500 mL round bottom flask, andheated in a nitrogen atmosphere for 15 hours to reflux the same toprepare a mixture. The mixture was added to 1,000 mL of methanol tofilter crystallized solids, dissolved in monochlorobenzene to filter thesame by using a silica gel/celite, a suitable amount of organic solventwas removed therefrom, and then the same was recrystallized withmethanol to obtain Compound 813 (11.7 g and yield 50%). Element analysisresults and NMR analysis results of Compound 813 are as follows.

calcd. C₄₀H₂₅N₃O: C, 85.24; H, 4.47; N, 7.46; O, 2.84; found C, 85.22;H, 4.46; N, 7.47; O, 2.83.

300 MHz (CDCl₃, ppm): δ 8.960 (m, 1H), 8.865 (m, 2H), 8.657 (dd, 1H),8.359 (dd, 2H), 8.196 (d, 2H), 8.081 (dd, 1H), 7.999 (d, 1H), 7.816 (t,1H), 7.659-7.727 (m, 2H), 7.381-7.601 (m, 10H), 7.316 (t, 2H)

Synthesis Example 2: Synthesis of Compound 814

15.0 g (31.4 mmol) of Intermediate C, 9.7 g (37.7 mmol) of5H-benzofuro[3,2-c]carbazole, 6.0 g (62.9 mmol) of sodium t-butoxide,2.9 g (3.1 mmol) of Pd(dba)₂, and 3.1 mL (6.3 mmol) of tri-t-butylphosphine (50% in toluene solution) were added to 125.7 mL of xylene ina 500 mL round bottom flask, and heated in a nitrogen atmosphere for 15hours to reflux the same to prepare a mixture. The mixture was added to1,000 mL of methanol to filter crystallized solids, dissolved indichlorobenzene to filter the same by using a silica gel/celite, asuitable amount of organic solvent was removed therefrom, and then thesame was recrystallized with methanol to obtain Compound 814 (11.8 g,yield 57%). Element analysis results and NMR analysis results ofCompound 814 are as follows.

calcd. C₄₆H₂₇N₃O₂: C, 84.51; H, 4.16; N, 6.43; O, 4.89; found C, 84.49;H, 4.17; N, 6.44; O, 4.87.

300 MHz (CDCl₃, ppm): δ 9.023 (t, 1H), 8.905-8.959 (m, 2H), 8.797 (dd,1H), 8.666 (dd, 1H), 8.392 (m, 2H), 8.110 (dd, 1H), 8.012 (m, 3H),7.684-7.884 (t, 4H), 7.362-7.627 (m, 12H)

Synthesis Example 3: Synthesis of Compound 815 Synthesis of IntermediateD

30.0 g (152.9 mmol) of Intermediate A, 30.4 g (152.9 mmol) of1-(3-bromophenyl)ethanone, and 6.1 g (152.9 mmol) of sodium hydroxidewere added to 458.7 mL of ethanol in a 1,000 mL round bottom flask andthen stirred in a nitrogen current for 2 hours at room temperature toprepare a mixture. Crystallized solids in the mixture were filtered toobtain Intermediate D (46.2 g, yield 80.0%). Element analysis results ofIntermediate D are as follows.

calcd. C₂₁H₁₃BrO₂: C, 66.86; H, 3,47; Br, 21.18; O, 8.48; found C,66.83; H, 3.45; Br, 21.17; O, 8.49.

Synthesis of Intermediate E

80.3 g (212.9 mmol) of Intermediate D, 40.0 g (255.4 mmol) ofbenzimidamide, and 17 g (425.7 mmol) of sodium hydroxide were added to1,000 ml of ethanol in a 2,000 mL round bottom flask and then heated ina nitrogen atmosphere for 15 hours to reflux the same to prepare amixture. Crystallized solids in the mixture were filtered and thenstirred with water to filter the same. The crystallized solids werestirred again with ethanol and then filtered to obtain Intermediate E(45.8 g, yield 45%). Element analysis results of Intermediate E are asfollows.

calcd. C₂₈H₁₇BrN₂O: C, 70.45; H, 3.59; Br, 16.74; N, 5.87; O, 3.35;found C, 70.44; H, 3.61; Br, 16.71; N, 5.84; O, 3.35.

Synthesis of Compound 815

34.3. g (71.8 mmol) of Intermediate E, 10.0 g (60.0 mmol) of9H-carbazole, 11.5 g (119.6 mmol) of sodium t-butoxide, 5.5 g (6.0 mmol)of Pd(dba)₂, and 2.9 mL (12.0 mmol) of tri-t-butyl phosphine (50% intoluene solution) were added to 239.2 mL of xylene in a 500 mL roundbottom flask and then heated in a nitrogen atmosphere for 15 hours toreflux the same to prepare a mixture. The mixture was added to 1,000 mLof methanol to filter crystallized solids, which were dissolved inmonochlorobenzene to be filtered by using a silica gel/celite, asuitable amount of organic solvent was removed therefrom and thenrecrystallized with methanol to obtain Compound 815 (22.2 g, yield 66%).Element analysis results and NMR analysis results of Compound 815 are asfollows.

calcd. C₄₀H₂₅N₃O: C, 85.24; H, 4.47; N, 7.46; O, 2.84; found C, 85.21;H, 4.47; N, 7.48; O, 2.86.

300 MHz (CDCl₃, ppm): δ 8.905 (s, 1H), 8.745 (m, 3H), 8.635 (t, 1H),8.473 (tt, 1H), 8.208 (d, 2H), 8.120 (dd, 1H), 8.016 (d, 1H),7.802-7.885 (m, 2H), 7.317-7.600 (m, 13H)

Synthesis Example 4: Synthesis of Compound 816

19.0 g (56.0 mmol) of Intermediate E, 12.0 g (46.6 mmol) of5H-benzofuro[3,2-c]carbazole, 6.7 g (70.0 mmol) of sodium t-butoxide,1.3 g (1.4 mmol) of Pd(dba)₂, and 2.1 mL (4.2 mmol) tri t-butylphosphine(50% in toluene) were added to 182.9 mL of xylene in a 500 mL roundbottom flask and then heated in a nitrogen atmosphere for 15 hours toreflux the same to prepare a mixture. The mixture was added to 1,000 mLof methanol to filter crystallized solids, dissolved in dichlorobenzeneto filter the same by using a silica gel/celite, a suitable amount oforganic solvent was removed therefrom, and then the same wasrecrystallized with methanol to obtain Compound 816 (14.7 g, yield 48%).Element analysis results and NMR analysis results of Compound 816 are asfollows.

calcd. C₄₆H₂₇N₃O₂: C, 84.51; H, 4.16; N, 6.43; O, 4.89; found C, 84.53;H, 4.18; N, 6.42; O, 4.87.

300 MHz (CDCl₃, ppm): δ 8.903 (s, 1H), 8.739 (d, 3H), 8.641 (t, 2H),8.506 (d, 1H), 8.096 (d, 1H), 7.976 (m, 3H), 7.868 (m, 2H), 7.763 (d,1H), 7.347-7.634 (m, 13H)

Synthesis Example 5: Synthesis of Compound 506

a) Synthesis of Intermediate 506-1

22.6 g (100 mmol) of 2,4-dichloro-6-phenyltriazine was added to 100 mLof tetrahydrofuran, 100 mL of toluene, and 100 mL of distilled water ina 500 mL round-bottom flask, and then, 0.9 equivalent weights ofdibenzofuran-3-boronic acid, 0.03 equivalent weights oftetrakistriphenylphosphine palladium, and 2 equivalent weights ofpotassium carbonate were added thereto, followed by heating whilerefluxing in a nitrogen atmosphere. After 6 hours, the reaction solutionwas cooled, the water layer was removed, and the organic layer was driedunder reduced pressure. The resulting solid was washed with water andhexane, and the solid was recrystallized by using 200 ml of toluene tocomplete the preparation of Intermediate 506-1 at a yield of 60%.

b) Synthesis of Compound 506

8.01 g (22.4 mmol) of Intermediate 506-1 synthesized above was added to80 mL of tetrahydrofuran and 40 mL of distilled water in a 500 mLround-bottom flask, and 1.0 equivalent weight of9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-carbazole(CAS: 785051-54-9), 0.03 equivalent weights oftetrakistriphenylphosphine palladium, and 2 equivalent weights ofpotassium carbonate were added thereto, followed by heating whilerefluxing in a nitrogen atmosphere. After 18 hours, the reactionsolution was cooled and the precipitated solid was filtered and washedwith 500 mL of water. The solid was recrystallized by using 500 mL ofmonochlorobenzene to complete the preparation of 10.12 g of Compound506.

LC/MS calculated for: C₃₉H₂₄N₄O Exact Mass: 564.1950 found for: 565.20.

Synthesis Example 6: Synthesis of Compound 825

Compound 825 was synthesized in the same manner as in the same manner asin “b)” of Synthesis Example 5, except that9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-carbazole(CAS: 870119-58-7) was used in an equivalent weight of 1.0 instead of9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-carbazole.

LC/MS calculated for: C₃₉H₂₄N₄O Exact Mass: 564.1950 found for: 565.20.

Comparative Synthesis Example 1: Synthesis of Comparative Compound R1

a) Synthesis of Intermediate R1-1

Intermediate R1-1 was synthesized in the same manner as in “b)” ofSynthesis Example 5, except that each of3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-dibenzofuran and1-bromo-4-chloro-benzene was used in an equivalent weight of 1 insteadof Intermediate 506-1 and9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-carbazole.

b) Synthesis of Intermediate R1-2

One equivalent weight of Intermediate R1-1 synthesized above was addedto 150 mL of xylene in a 500 mL round-bottom flask, and 0.05 equivalentweights of dichlorodiphenylphosphinoferrocene palladium, 1.2 equivalentweights of bis(pinacolato)diboron, and 2 equivalent weights of potassiumacetate were added thereto, followed by heating while refluxing for 18hours in a nitrogen atmosphere. After cooling the reaction solution, theresultant solution was washed with water through extraction, the organiclayer was treated with activated carbon and filtered through silica gel,and the filtrate was concentrated. The concentrated solid was stirredwith a small amount of hexane, and then the solid was filtered therefromto complete the preparation of Intermediate R1-2 at a yield of 75%.

c) Synthesis of Intermediate R1-3

Intermediate R1-3 was synthesized in the same manner as in “a)” ofSynthesis Example 5, except that 0.9 equivalent weights of[4-(9H-carbazol-9-yl)phenyl]boronic acid was used instead ofdibenzofuran-3-boronic acid.

d) Synthesis of Comparative Compound R1

Comparative Compound R1 was synthesized in the same manner as in “a)” ofSynthesis Example 5, except that Intermediate R1-2 and Intermediate R1-3was used in an equivalent weight of 1 instead of2,4-dichloro-6-phenyltriazine and dibenzofuran-3-boronic acid.

LC/MS calculated for: C₄₅H₂₈N₄O Exact Mass: 640.2263 found for: 641.23.

Comparative Synthesis Example 2: Synthesis of Comparative Compound R2

a) Synthesis of Intermediate R2-1

Intermediate R2-1 was synthesized in the same manner as in “a)” ofSynthesis Example 5, except that 2,4-dichloro-6-phenylpyrimidine wasused in an equivalent weight of 1 instead of2,4-dichloro-6-phenyltriazine.

b) Synthesis of Comparative Compound R2

Comparative Compound R2 was synthesized in the same manner as in “b)” ofSynthesis Example 5, except that each of Intermediate R2-1 synthesizedabove was used in an equivalent weight of 1.0 instead of Intermediate506-1.

LC/MS calculated for: C₄₀H₂₅N₃O Exact Mass: 563.1998 found for: 564.23.

Comparative Synthesis Example 3: Synthesis of Comparative Compound R3

a) Synthesis of Intermediate R3-1

In a nitrogen atmosphere, 7.86 g (323 mmol) of magnesium and 1.64 g(6.46 mmol) of iodine were added to 0.1 L of tetrahydrofuran (THF) andstirred for 30 minutes, and then, 80 g (323 mmol) of 3-bromodibenzofurandissolved in 0.3 L of THF was slowly added dropwise thereto at atemperature of 0° C. for 30 minutes. The resulting mixed solution wasslowly added dropwise to 29.5 g (160 mmol) of cyanuric chloridedissolved in 0.5 L of THF at a temperature of 0° C. for 30 minutes. Thereaction temperature was raised to room temperature, followed by 1 hourof stirring. Then, in the refluxing condition, the resultant solutionwas additionally stirred for 12 hours. After cooling the reactionmixture, water was added slowly to terminate the reaction, and theorganic solvent was concentrated under reduced pressure to obtain asolid. This was stirred with 200 mL of acetone and then filtered tocomplete the preparation of Intermediate R3-1 at a yield of 40%.

b) Synthesis of Comparative Compound R3

Comparative Compound R3 was synthesized in the same manner as in “b)” ofSynthesis Example 5, except that each of Intermediate R3-1 synthesizedabove was used in an equivalent weight of 1.0 instead of Intermediate506-1.

LC/MS calculated for: C₄₅H₂₆N₄O₂ Exact Mass: 654.2056 found for:655.2089.

Evaluation Example 1: Evaluation of HOMO, LUMO, and Triplet (T1) EnergyLevels of Compounds

HOMO, LUMO, and triplet (T1) energy levels of Compounds 813 to 824 wereevaluated by using a DFT method of a Gaussian program (optimized atB3LYP and 6-31G(d,p) levels) and the results obtained therefrom areshown in Table 1 below.

TABLE 1 Compound No. HOMO (eV) LUMO (eV) T₁ energy level (eV) 813 −5.236−1.880 2.994 815 −5.355 −1.802 3.096 817 −5.252 −1.877 3.002 819 −5.435−1.894 3.089 814 −5.150 −1.894 2.9 816 −5.344 −1.909 3.02 820 −5.303−1.925 2.959 818 −5.139 −1.885 2.904 821 −5.188 −1.893 2.945 822 −5.350−1.934 2.997 823 −5.206 −1.897 2.951 824 −5.394 −1.913 3.063

Thereafter, HOMO, LUMO, S1 energy level, and T1 energy level ofCompounds 813 to 816 obtained according to the method in Table 2 and theresults thereof are shown in Table 3.

TABLE 2 An evaluation Each compound was diluted in CHCl₃ at aconcentration of 1 × 10⁻⁵M to method of a HOMO measure UV absorptionspectrum by using a Shimadzu UV-350 Spectrometer energy level at roomtemperature and then a HOMO energy level was calculated by using anoptical band gap (Eg) from an edge of the absorption spectrum. Anevaluation Cyclic voltammetry (CV) (electrolyte: 0.1M Bu₄NClO₄/solvent:CH₂Cl₂/ method of a LUMO electrode: a 3-electrode system (workingelectrode: GC, standard electrode: energy level Ag/AgCl, and supplyelectrode: Pt)) was used to obtain a voltage (V)-current (A) graph foreach compound and a LUMO energy level was calculated from a reductiononset of the graph. An evaluation A mixture of toluene and each compound(1 mg of each compound was method of evT1 dissolved in 3 cc of toluene)was added to a quartz cell and liquid nitrogen (77 K) energy level wasadded thereto, a photoluminescence measurement device was used tomeasure photoluminescence spectrum, which was compared to a conventionalroom temperature photoluminescence spectrum to only analyze the peakobserved only at low temperature and calculate a T1 energy level.

TABLE 3 Compound No. HOMO (eV) LUMO (eV) T1 energy level (eV) 813 −5.432−1.901 2.994 815 −5.665 −1.972 3.096 814 −5.451 −1.998 2.9 816 −5.643−1.942 3.02

It may be concluded from Tables 1 and 3 that the condensed-cycliccompounds have suitable electrical properties to be used as a materialfor an organic light-emitting device.

Evaluation Example 2: Evaluation of Thermal Properties of SynthesizedCompounds

compounds 813 to 816 were subjected to thermal analyses by using ThermoGravimetric Analysis (TGA) and Differential Scanning calorimetry (DSC)(N₂ atmosphere and temperature range for TGA: room temperature ˜800° C.(10° C./min), for DSC: from room temperature to 400° C., Pan Type: forTGA: Pt Pan in a disposable Al Pan, for DSC: a disposable Al pan) andresults obtained therefrom are shown in Table 4. From Table 4, it may beconcluded that Compounds 813 to 816 have excellent thermal stabilities.

TABLE 4 Compound No. Tc (° C.) Tm (° C.) Tg (° C.) 813 — — 101.21 815218.72 241.72 102.57 814 — 312.38 — 816 — — 139.38

Example 1

An ITO glass substrate was cut to a size of 50 mm×50 mm×0.5 mm, and theITO glass substrate was ultrasonically washed using isopropyl alcoholand pure water for 15 minutes each, followed by irradiation of UV andexposure to ozone for cleaning for about 30 minutes.

m-MTDATA was vacuum deposited on the ITO glass substrate to form an HILhaving a thickness of 600 Å, and α-NPB was vacuum deposited at a rate of1 Å/sec on the HIL to form an EML having a thickness of 300 Å.Thereafter, Ir(ppy)₃ (dopant) and Compound 813 (host) were co-depositedat a rate of 0.1 Å/sec and 1 Å/sec, respectively, on the HTL to form anEML having a thickness of 400 Å. BAlq was vacuum deposited on the EML ata rate of 1 Å/sec to form an HBL having a thickness of 50 Å and thenAlq₃ was vacuum deposited on the HBL to form an ETL having a thicknessof 300 Å. Then, LiF 10 Å (EIL) and Al 2000 Å (cathode) were sequentiallyvacuum deposited on the ETL to manufacture an organic light-emittingdevice.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 815 was used as a host instead ofCompound 813 when forming an EML.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 814 was used as a host instead ofCompound 813 when forming an EML.

Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 816 was used as a host instead ofCompound 813 when forming an EML.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound A was used as a host instead ofCompound 813 when forming an EML.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound B was used as a host instead ofCompound 813 when forming an EML.

Comparative Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound C was used as a host instead ofCompound 813 when forming an EML.

Evaluation Example 2: Evaluation of Characteristics of OrganicLight-Emitting Device

Changes in current density and brightness, and emission efficiency ofeach organic light-emitting device manufactured in Examples 1 to 4 andComparative Examples 1 to 3 were measured. A detailed method ofmeasurement is as described below and results obtained therefrom areshown in Table 5 below:

(1) Measurement of Changes in Current Density According to Changes inVoltage

For each organic light-emitting device, voltage was increased from 0volts (V) to 10 V to measure current that flows through a unit celltherein by using a voltage-current meter (Keithley 2400) and the currentwas divided by surface area to obtain a current density.

(2) Measurement of Changes in Brightness According to Changes in Voltage

For each organic light-emitting device, brightness was measured whileincreasing voltage from 0 V to 10 V to by using Cs-1000A (a product ofMinolta).

(3) Measurement of Emission Efficiency

Brightness, current density, and voltage measured from (1) and (2) wereused to calculate current efficiency (candelas per ampere (cd/A)) at thesame current density (10 milliamperes per square centimeter (mA/cm²)).

TABLE 5 Driving Current voltage density Brightness Host Dopant (V)(cd/A) (cd/m²) Example 1 Compound 813 Ir(ppy)₃ 3.7 40.3 3500 Example 2Compound 815 Ir(ppy)₃ 3.4 46.2 3500 Example 3 Compound 814 Ir(ppy)₃ 4.136.1 3500 Example 4 Compound 816 Ir(ppy)₃ 3.8 33.8 3500 ComparativeCompound A Ir(ppy)₃ 4.4 32.6 3500 Example 1 Comparative Compound BIr(ppy)₃ 4.3 31.5 3500 Example 2 Comparative Compound C Ir(ppy)₃ 4.232.9 3500 Example 3

From Table 5, it may be concluded that the organic light-emittingdevices of Examples 1 to 4 have lower driving voltage, high efficiency,and high brightness compared the organic light-emitting devices ofComparative Examples 1 to 3.

Examples 5 and 6

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound 506 and 825, respectively, was usedas a host instead of Compound 813 when forming an EML.

Comparative Examples R1 to R3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Compound R1 to R3, respectively, was used as ahost instead of Compound 813 when forming an EML.

Evaluation Example 3

Driving voltage, luminous power efficiency and lifespan (T90@24K) ofeach organic light-emitting device manufactured in Example 5 andComparative Example R1 were measured. A detailed method of measurementis as described below and results obtained therefrom are shown as arelative value (%) in Table 6 below. The relative value of the drivingvoltage, the luminous power efficiency and the lifespan of the organiclight-emitting device of Comparative Example R1 were regarded as “100%.”

(1) Measurement of Current Density Change Depending on Voltage Change

Current values flowing in the unit device of the manufactured organiclight emitting diodes were measured for, while increasing the voltagefrom 0 V to 10 V using a current-voltage meter (Keithley 2400), and themeasured current values were divided by an area to provide the results.

(2) Measurement of Luminance Change Depending on Voltage Change

Luminance of the manufactured organic light emitting diodes was measuredfor luminance, while increasing the voltage from 0 V to 10 V using aluminance meter (Minolta Cs-1000A).

(3) Measurement of Luminous Power Efficiency

Luminous Power efficiency (Im/W) at the same current density (10 mA/cm²)was calculated by using the luminance, current density, and voltages (V)from the items (1) and (2).

(4) Measurement of Driving Voltage

Driving voltages (V) of each device were measured at 15 mA/cm² using acurrent-voltage meter (Keithley 2400).

(5) Measurement of Lifespan (T90@24K)

T₉₀ was measured an amount of time that lapsed when 100% of the initialluminance (2400 cd/m²) was decreased to 90% at 24K using a Polanonixlife-span measurement system.

TABLE 6 Luminous Power T₉₀@24K Driving voltage Efficiency (relative Host(relative value) (relative value) value) Example 5 Compound 506  91%137% 288% Comparative Comparative 100% 100% 100% Example R1 Compound R1

 

From Table 6, it may be concluded that the organic light-emitting deviceof Example 5 has lower driving voltage, higher luminous powerefficiency, and longer lifespan compared the organic light-emittingdevices of Comparative Example R1.

Evaluation Example 4

Driving voltage and lifespan (T90@24K) of each organic light-emittingdevice manufactured in Example 6 and Comparative Example R2 weremeasured. A detailed method of measurement is as described in EvaluationExample 3 and results obtained therefrom are shown as a relative value(%) in Table 7 below. The relative value of the driving voltage and thelifespan of the organic light-emitting device of Comparative Example R2were regarded as “100%.”

TABLE 7 Driving voltage T₉₀@24K Host (relative value) (relative value)Example 6 Compound 825  96% 162% Comparative Comparative 100% 100%Example R2 Compound R2

 

From Table 7, it may be concluded that the organic light-emitting deviceof Example 6 has lower driving voltage, and longer lifespan compared theorganic light-emitting devices of Comparative Example R2.

Evaluation Example 5

Driving voltage and lifespan (T90@24K) of each organic light-emittingdevice manufactured in Example 6 and Comparative Example R3 weremeasured. A detailed method of measurement is as described in EvaluationExample 3 and results obtained therefrom are shown as a relative value(%) in Table 8 below. The relative value of the driving voltage and thelifespan of the organic light-emitting device of Comparative Example R3were regarded as “100%.”

TABLE 8 Driving voltage T₉₀@24K Host (relative value) (relative value)Example 6 Compound 825 105% 141% Comparative Comparative 100% 100%Example R3 Compound R3

 

From Table 8, it may be concluded that the organic light-emitting deviceof Example 6 has longer lifespan compared the organic light-emittingdevices of Comparative Example R2.

As described above, according to the one or more of the aboveembodiments, the condensed-cyclic compound have excellent electricalproperties and thermal stability and thus, an organic light-emittingdevice including the condensed-cyclic compound may have low drivingvoltage, high efficiency, high brightness, and a long lifespan.

It should be understood that the exemplary embodiments described thereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

While one or more embodiments have been described with reference to theFIGURES, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope of the present disclosure as definedby the following claims.

What is claimed is:
 1. A condensed-cyclic compound represented byFormula 1A:

wherein in Formula 1A, ring A₁ is represented by Formula 1D;

X₁ to X₃ is N; X₄ is O or S; L₄ and L₂₁ are each independently selectedfrom groups represented by Formulae 2-1, 2-2 and 2-34;

wherein in Formulae 2-1, 2-2 and 2-34, Z₁ is selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group and a phenyl group and d1 is selected from integersof 1 to 4; a4 is selected from integers 0 to 3 and a21 is 0, 1, 2 or 3;R₅, R₆, R₁₅ and R₁₇ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, anda C₁-C₂₀ alkoxy group; R₄ is selected from: a phenyl group; and a phenylgroup, substituted with at least one of a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group,and a biphenyl group; b4 to b6, b15 and b17 are each independentlyselected from integers of 1 to
 3. 2. The condensed-cyclic compound ofclaim 1, wherein the condensed-cyclic compound is represented by one ofFormulae 1A(1) to 1A(4):

wherein in Formulae 1A(1) to 1A(4), descriptions of ring A₁, X₁ to X₄,L₄, L₂₁, a1, a21, R₄ to R₆, R₁₅, R₁₇, b4 to b6, b15 and b17 are the sameas described in claim
 1. 3. The condensed-cyclic compound of claim 1,wherein a21 is 0, 1 or
 2. 4. The condensed-cyclic compound of claim 1,wherein the condensed-cyclic compound is one of Compounds 1, 85, 169,253, 337, 421, 505, 506, 575, 659, 660, 729 and 825:


5. An organic light-emitting device comprising a first electrode; asecond electrode; and an organic layer disposed between the firstelectrode and the second electrode, wherein the organic layer comprisesan emission layer and the condensed-cyclic compound of claim
 1. 6. Theorganic light-emitting device of claim 5, wherein the first electrode isan anode and the second electrode is a cathode, wherein the organiclayer comprises i) a hole transport region disposed between the firstelectrode and the emission layer, wherein the hole transport regioncomprises at least one of a hole-injection layer, a hole-transportinglayer, and an electron-blocking layer; and ii) an electron transportregion disposed between the emission layer and the second electrode,wherein the electron transport region comprises at least one layerselected from a hole-blocking layer, an electron-transporting layer, andan electron-injecting layer.
 7. The organic light-emitting device ofclaim 5, wherein the emission layer comprises the condensed-cycliccompound.
 8. The organic light-emitting device of claim 7, wherein theemission layer further comprises an organometallic compound representedby Formula 81:

wherein in Formula 81, M is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu,Tb, and Tm; Y₁ to Y₄ are each independently C or N; Y₁ and Y₂ areconnected by a single bond or a double bond and Y₃ and Y₄ are connectedby a single bond or a double bond; CY₁ and CY₂ are each independentlyselected from a benzene, a naphthalene, a fluorene, a spiro-fluorene, anindene, a pyrrole, a thiopene, a furan, an imidazole, a pyrazole, athiazole, an isothiazole, an oxazole, an isooxazole, a pyridine, apyrazine, a pyrimidine, a pyridazine, a quinoline, an isoquinoline, abenzoquinoline, a quinoxaline, a quinazoline, a carbazole, abenzoimidazole, a benzofuran, a benzothiopene, an isobenzothiopene, abenzooxazole, an isobenzooxazole, a triazole, a tetrazole, anoxadiazole, a triazine, a dibenzofuran, and a dibenzothiopene, whereinCY₁ and CY₂ are optionally bound to each other by a single bond or anorganic linking group; R₈₁ and R₈₂ are each independently selected froma hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,—SF₅, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic hetero-condensedpolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇); a81 anda82 are each independently selected from integers of 1 to 5; n81 isselected from integers of 0 to 4; n82 is 1, 2, or 3; and L₈₁ is selectedfrom a monovalent organic ligand, a divalent organic ligand, and atrivalent organic ligand.